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Novel Reductive Amination of Nitriles: An Efficient Route to 5‐Hydroxypiperidone‐Derived N , N ‐Acetals
Author(s) -
Vink Mandy K. S.,
Schortinghuis Christien A.,
MackovaZabelinskaja Antonina,
Fechter Martin,
Pöchlauer Peter,
Castelijns A. Marianne C. F.,
van Maarseveen Jan H.,
Hiemstra Henk,
Griengl Herfried,
Schoemaker Hans E.,
Rutjes Floris P. J. T.
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200390054
Subject(s) - chemistry , cyanohydrin , reductive amination , amination , enantioselective synthesis , nitrile , organic chemistry , alkylation , bicyclic molecule , combinatorial chemistry , catalysis
5‐Hydroxypiperidin‐2‐one is a versatile building block for the preparation of potentially biologically active compounds. We detail an enantioselective biocatalytic approach towards its synthesis using ( S )‐hydroxynitrile lyase (HNL)‐mediated cyanohydrin formation, followed by hydrogenation. By adjusting the conditions of the latter step, we were able to obtain 5‐hydroxypiperidinone‐derived (bicyclic) N , N ‐acetals via an unprecedented reductive amination of the nitrile group, as well as form N ‐alkylated 5‐hydroxypiperidinone in a single step from the same cyanohydrin intermediate.